A novel and efficient synthesis of 3,3-disubstituted indol-2-ones via Passerini three-component reactions in the presence of 4 Å molecular sieves

被引:9
|
作者
Esmaeili, Abbas Ali [1 ,2 ]
Ghalandarabad, Saeid Amini [1 ]
Jannati, Saeideh [1 ]
机构
[1] Univ Birjand, Fac Sci, Dept Chem, Birjand, Iran
[2] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Iran
关键词
Isatin; Isocyanide; Passerini coupling reaction; Carboxylic acid; 3,3-Disubstituted indol-2-ones; DIALKYL ACETYLENEDICARBOXYLATES; CYANOHYDRIN ESTERS; BENZOYL CYANIDE; ALDEHYDES; ISOCYANIDES; CONVENIENT; CHEMISTRY; ISATINS; KETONES;
D O I
10.1016/j.tetlet.2012.11.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Passerini coupling of cyclohexylisocyanide with isatins and carboxylic acids in the presence of 4 angstrom molecular sieves is described. This process offers a highly efficient and atom-economic access to 3-acyloxy-3-carboxamido-1,3-dihydro-2H-indol-2-ones in high to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:406 / 408
页数:3
相关论文
共 50 条
  • [21] Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
    Peng, Jin-Bao
    Geng, Hui-Qing
    Wang, Wei
    Qi, Xinxin
    Ying, Jun
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2018, 365 : 10 - 13
  • [22] Three-Component Reaction for the Convenient Synthesis of Functionalized 3-{1-[2-(1H-Indol-3-yl) ethyl]-4,5,6,7-tetrahydro-1H- indol-3-yl} indolin-2-ones
    Jiang, Yan-Hong
    Yan, Chao-Guo
    SYNTHESIS-STUTTGART, 2016, 48 (18): : 3057 - 3064
  • [23] Nickel-catalyzed One-pot, Three-component Synthesis of 3,4-disubstituted Isoxazole-5(4H)-ones in Aqueous Medium
    Kiyani, Hamzeh
    Samimi, Heshmat Allah
    CHIANG MAI JOURNAL OF SCIENCE, 2017, 44 (03): : 1011 - 1021
  • [24] Ultrasound-promoted synthesis of 3-[(acetamido)(aryl)methyl]-4-hydroxy-6-methyl-2H-pyran-2-ones via a three-component condensation
    Bizhanpoor, Nafiseh
    Hassanabadi, Alireza
    JOURNAL OF CHEMICAL RESEARCH, 2016, (01) : 38 - 39
  • [25] Synthesis of 2,3,5,6-tetrasubstituted pyridines via selective three-component reactions of aldehyde and two different enaminones
    Li, Yi
    Wang, Guodong
    Hao, Guifeng
    Wan, Jie-Ping
    TETRAHEDRON LETTERS, 2019, 60 (03) : 219 - 222
  • [26] Three-component synthesis of novel spiro[4H-pyran-3,3′-oxindoles] using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione
    Zafari, Parvin
    Saatluo, Bahman Ebrahimi
    Rashidi, Ahmad
    Baradarani, Mehdi M.
    Joule, John A.
    ARKIVOC, 2021, : 9 - 16
  • [27] An efficient diastereoselective synthesis of spiro pyrido[2,1-b][1,3]oxazines via a novel pyridine-based three-component reaction
    Esmaeili, Abbas Ali
    Vesalipoor, Hamid
    Hosseinabadi, Rahele
    Zavareh, Alireza Fakhari
    Naseri, Mohammad Ali
    Ghiamati, Ebrahim
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4865 - 4867
  • [28] Asymmetric synthesis of spiro[4H-chromene-3,3′-oxindoles] via a squaramide-organocatalytic three-component cascade Knoevenagel/Michael/cyclization sequence
    Wang, Liming
    Mu, Hongwen
    Sun, Yuhong
    Jin, Ying
    Zhang, Wei
    MOLECULAR DIVERSITY, 2025, 29 (01) : 293 - 302
  • [29] Efficient synthesis of substituted 2-(4H-1,3-benzoxazin-2-yl) phenols via a pseudo three-component reaction
    Wang, Ting
    Dai, Chenlu
    Qing, Xushun
    Wang, Cunde
    JOURNAL OF CHEMICAL RESEARCH, 2018, (03) : 121 - 124
  • [30] A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides
    Shaabani, Ahmad
    Soleimani, Ebrahim
    Sarvary, Afshin
    Rezayan, Ali Hossein
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) : 3968 - 3970